THE NITROPYRIDINE GROUP

Background

In heterocyclic chemistry pyridines are essential, being one of the most abundant and best known groups of aromatic heterocycles. The pyridine ring system is incorporated into the structure of pharmaceuticals, natural products, agrochemicals, ligands in transition metal catalyst complexes and commercial products. A variety of synthetic methods involving pyridine chemistry have therefore been developed.

Unfortunately, one of the most important classes of aromatic reactions, electrophilic aromatic substitution, takes place with great difficulty due to the electron deficient nature of the pyridine ring. The direct nitration of unactivated pyridine compounds has been almost impossible until recently. However, a number of substituted 3-nitropyridines are now readily available through prof. Bakke’s improved nitration method [ref]. References:

Synthetic applications of nitropyridine derivatives

Keeping in mind the importance and useful properties of many pyridine-based compounds, the improved nitration method providesnew possibilities in heterocyclic chemistry. The present research activity is a continuation of prof. em. Bakke’s research on nitropyridines at Department of chemistry, NTNU.

Nitropyridine derivatives are suitable substrates for the preparation of new heterocyclic products; many of these heterocyclic systems may have biological activity.

• We  are investigating the chemistry of nitropyridine derivatives
• We utilize nitropyridines derivatives as substrates for the formation of new products, including bis-heterocyclic compounds.
• We are developing new synthetic routes to fused heterocycles.

We have synthesised a number of new products, including new bis-heterocycles and new ring systems. The following topics have been studied:

• New stable pyridyl isocyanates
• 1,3 Dipolar cycloadditions of pyridyl isocyanates
• Triazolopyridine derivatives
• Cyclic urea, imidazopyridinone
• Nucleophilic aromatic substitution of the nitro group
• Pyridyl malonate chemistry
• β-Carboline analogues and pyridazines
• Palladium complexes
• Biological activity